NOTICE: Summary decisions issued by the Appeals Court pursuant to M.A.C. Rule 23.0, as appearing in 97 Mass. App. Ct. 1017 (2020) (formerly known as rule 1:28, as amended by 73 Mass. App. Ct. 1001 [2009]), are primarily directed to the parties and, therefore, may not fully address the facts of the case or the panel's decisional rationale. Moreover, such decisions are not circulated to the entire court and, therefore, represent only the views of the panel that decided the case. A summary decision pursuant to rule 23.0 or rule 1:28 issued after February 25, 2008, may be cited for its persuasive value but, because of the limitations noted above, not as binding precedent. See Chace v. Curran, 71 Mass. App. Ct. 258, 260 n.4 (2008).
COMMONWEALTH OF MASSACHUSETTS
APPEALS COURT
23-P-630
COMMONWEALTH
vs.
EMMANUEL T. BILE, JR.
MEMORANDUM AND ORDER PURSUANT TO RULE 23.0
A Superior Court jury convicted the defendant of two counts
of aggravated rape.1 The defendant now appeals from the denial
of his motion for a new trial claiming, inter alia, that his
trial counsel was ineffective in failing to file a motion to
suppress text messages recovered from his cell phone.
Specifically, the defendant argues that the police, after
seizing his phone without his consent, unreasonably delayed for
forty days in obtaining a search warrant for his phone. We
1On direct appeal, the defendant claimed error in the denial of his motion to suppress a recorded statement, jury selection, several evidentiary rulings, jury instructions, the prosecutor's closing argument, and the denial of his motion to continue. In May 2020, a panel of this court affirmed his convictions. See Commonwealth v. Bile, 97 Mass. App. Ct. 1120 (2020). conclude that the defendant has demonstrated a likelihood that a
motion to suppress would have been successful because the
police's delay in obtaining a warrant was unreasonable given the
defendant's strong possessory interest in his phone. We also
conclude that there is a reasonable probability the verdict
would have been different had the text messages retrieved from
the defendant's cell phone been excluded from his trial.
Accordingly, we reverse and remand for a new trial.2
Background. We summarize the facts presented to the jury,
reserving additional facts for later discussion. The
convictions stemmed from allegations of nonconsensual sexual
conduct that occurred at a University of Massachusetts (UMass)
dormitory. On the evening of October 12, 2012, the victim, a
first-year student at UMass, became very intoxicated after
drinking alcohol with her friends in her dormitory. Between
midnight and 1 A.M., the defendant, Adam Liccardi, Justin King,
and Caleb Womack, who were acquaintances of the victim and did
not attend UMass, arrived uninvited at her dormitory.3 The four
2 Because we conclude that the defendant's ineffective assistance of counsel claim requires reversal, we need not reach the remaining claims raised on appeal.
3 All four men were indicted for raping the victim. Following separate jury trials, Adam Liccardi was convicted of two counts of aggravated rape and one count of rape, and Justin King was convicted of three counts of aggravated rape. Caleb
2 men partied in the victim's room with the victim and two of her
friends who lived on the same floor of the dormitory. At one
point, the victim became so intoxicated that she could not stand
up without assistance. In response to her condition, the
victim's friends assisted the victim getting into her bed and
told the defendant, Liccardi, King, and Womack that it was time
to leave the victim's room. Despite this directive, Liccardi
and King remained in the victim's room, and the defendant, along
with Womack, returned to her room soon after the victim's
friends had departed. The four men then engaged in sexual acts
with the victim while she was in and out of consciousness. The
defendant later admitted that he penetrated the victim's vagina
with his penis.4 When the victim began to cry loudly, the
defendant, King, and Womack stopped and left her room. Liccardi
remained with her and sought to console her before sexually
assaulting her again.
The next morning, on October 13, the victim, who was
visibly upset and bruised, told one of the friends who had
Womack pleaded guilty to reduced charges of rape and indecent assault and battery.
4 The defendant, during his interview with the police On October 17, 2012, admitted that he penetrated the victim's vagina with both his penis and finger, and anally with his finger. At trial, the defendant testified that he only penetrated the victim's vagina.
3 assisted her the night before that she had been repeatedly raped
by the four men. On the morning of October 15, 2012, the victim
reported the assault to UMass police. The victim allowed the
police to view her phone after telling them that she had
communicated with the defendant through text messages in the
days following the rape. The police then took photographs of
text messages displayed on the victim's phone, between the
victim and the defendant. On the same day, the victim underwent
a sexual assault nurse examination at a nearby hospital. The
subsequent examination of sperm samples from an external genital
swab and vaginal swab taken from the victim showed a match with
the defendant's DNA.
On October 17, the UMass police interviewed the defendant.
During the interview, the defendant stated he had what he
believed to be consensual sex with the victim. He described how
he and the three other men "took turns" engaging in sexual acts
with the victim. The defendant claimed it was consensual but
admitted the incident was out of character for the victim. He
described her condition as being "drunk," but not so intoxicated
that she could not consent to the encounter. The defendant
admitted that he responded to the victim's text messages to him
the following day. He also admitted that he sent text messages
to King, Liccardi, and Womack concerning the victim's allegation
4 that they had sexually abused her. When the police asked the
defendant to see his phone, the defendant declined to show it to
them. However, at the end of the interview, the police seized
the defendant's phone without either a warrant or his consent.
On November 26, forty days later, the police applied for and
received a search warrant for the cell phone.
The search of the defendant's phone yielded text messages
between the defendant and the victim,5 and between the defendant
and his codefendants; ninety-eight of these messages were
admitted at trial. For example, on the morning after the
alleged rape, the victim sent a text message to the defendant,
"You fucking brought them and didn't stop it. I'm fucking
bleeding internally." The defendant responded by messaging the
victim, "I'm sorry. I shouldn't have let that happen" and "I
failed you as a good friend and I'm sorry."
In another text message to the defendant, the victim
demanded five hundred dollars from the defendant and the other
men, warning the defendant that she would "tak[e] you all to
court" if they did not pay her. The defendant responded to the
victim's demand for five hundred dollars by texting, "[I']ll
talk to everyone and get [you] the money." Approximately one
As noted supra, the victim had previously shared the texts 5
between her and the defendant with police.
5 hour later, the defendant sent a text message to King saying,
"Call me after work we have to talk." The next day, on October
14, the defendant sent a text message to Womack asking him to
meet in person. And, on October 15, the defendant sent a text
message to Liccardi and stating that they needed to talk about
"what [the victim] wants to do to us." When Liccardi asked if
they were "beat," the defendant replied, "We aren't beat . . .
she tried blackmailing us so that's our defense."
On October 15, King sent a text message to the defendant
and asked, "What if they have cameras in the hallways?" and the
defendant replied, "Let's hope they don't." During the
following two days, the defendant and King exchanged text
messages about trying to convince Liccardi and Womack to pay the
victim the money she requested to avoid criminal charges. The
defendant communicated that they needed to do something to take
care of "the [victim] situation." In one exchange, the
defendant agreed with King that they were "fucked" if the victim
took them to court, that they "all" had to talk to get "rid of
this problem as fast as possible," and that they should pay the
victim whatever money she demanded.
The defendant's trial counsel did not move to suppress
these text communications as fruits of an unlawful search and
seizure of the defendant's phone.
6 Discussion. When a defendant moves for a new trial based
on ineffective assistance of counsel, the defendant must
demonstrate (1) performance on the part of counsel falling
measurably below that of an ordinary, fallible attorney, that
(2) effectively deprived the defendant of a substantial ground
of defense. See Commonwealth v. Saferian, 366 Mass. 89, 96
(1974). When a defendant asserts a claim of ineffective
assistance based on counsel's failure to file a motion to
suppress, "the defendant has to demonstrate a likelihood that
the motion to suppress would have been successful."
Commonwealth v. Comita, 441 Mass. 86, 91 (2004). In addition,
the defendant must show prejudice, that is, "a 'reasonable
probability' that, 'but for counsel's unprofessional errors, the
result of the proceeding would have been different.'"
Commonwealth v. Mahar, 442 Mass. 11, 15 (2004), quoting
Strickland v. Washington, 466 U.S. 668, 694 (1984). See Comita,
supra at 90, quoting Kimmelman v. Morrison, 477 U.S. 365, 375
(1986). We review the denial of a motion for new trial for an
abuse of discretion or any other error of law. See Commonwealth
v. Lane, 462 Mass. 591, 597 (2012).
1. Likelihood of suppression motion's success. Police may
retain an item seized without a warrant for "the relatively
short period of time needed . . . to obtain a search warrant,"
7 but must release the item if a warrant is not obtained within
that period (citation omitted). Commonwealth v. Gentile, 437
Mass. 569, 573, 575 (2002). For this reason, once a warrantless
seizure has been executed, the police "must make it a priority
to secure a search warrant that complies with the Fourth
Amendment." Commonwealth v. White, 475 Mass. 583, 593 (2016),
quoting United States v. Burgard, 675 F.3d 1029, 1035 (7th
Cir.), cert. denied, 568 U.S. 852 (2012). If the police fail to
do so, the seizure, even if "reasonable at its inception because
based upon probable cause[,] may become unreasonable as a result
of its duration." Segura v. United States, 468 U.S. 796, 812
(1984).
"[T]here is no bright-line rule that demarcates when a
delay is unreasonable." Commonwealth v. Cruzado, 480 Mass. 275,
283 (2018). Rather, the inquiry involves "balanc[ing] the
nature and quality of the intrusion on the individual's Fourth
Amendment interests against the importance of the governmental
interests alleged to justify the intrusion" (citation omitted).
White, 475 Mass. at 593-594. "'[C]ourts have identified several
factors highly relevant to this inquiry,' among them, and of
particular importance here, whether police acted 'diligen[tly]
in obtaining the warrant.'" Id. at 594, quoting United States
v. Laist, 702 F.3d 608, 613-614 (11th Cir. 2012).
8 A reasonable delay in obtaining a search warrant may be
justified by a strong government interest. See Cruzado, 480
Mass. at 284 (Commonwealth's interest in defendant's phone was
strong and justified ten-day delay in seeking search warrant
where "police had probable cause to believe that evidence
critical to a recent murder was present on the cell phone").
See also Illinois v. McArthur, 531 U.S. 326, 332–333 (2001)
(reasonable to prevent suspect from entering home for two hours
while police obtained warrant); United States v. Van Leeuwen,
397 U.S. 249, 252–253 (1970) (reasonable for police to seize
package for twenty-nine hours while seeking warrant).
In assessing the reasonableness of the delay, though, a
strong government interest in the property may be outweighed by
other factors such as lack of diligence in obtaining a warrant,
and a defendant's strong possessory interest in the property.
See White, 475 Mass. at 590, 595. See also United States v.
Pratt, 915 F.3d 266, 271-272 (4th Cir. 2019). The court's
reasoning in Pratt is instructive to the instant case. In that
case, the court held that a thirty-one day delay in obtaining a
warrant for a defendant's cell phone was unreasonable even after
determining that the government had a strong evidentiary
interest in the phone because the defendant, who was being
investigated for running a prostitution ring, admitted it
9 contained nude pictures of an underage sex worker. Id. at 270-
272. The court concluded that the government's strong interest
in the phone did not outweigh the defendant's "undiminished
possessory interest" because "[h]e didn't consent to its seizure
or voluntarily share the phone's contents." Id. at 272.
Further, the defendant's phone did not have evidentiary value
independent of its contents that would justify its indefinite
seizure. Id. at 273. Cf. Commonwealth v. Arthur, 94 Mass. App.
Ct. 161, 165 (2018) (cell phones' located in separate cars at
crime scene of coordinated shooting provided independent
evidentiary value on question of joint venture). Given the
defendant's "undiminished interest" in the phone, the court
reasoned that by not taking steps to obtain a warrant for
thirty-one days, the government had not acted with diligence and
the delay was unreasonable. See Pratt, 915 F.3d at 273.
Here, like in Pratt, the government had a strong interest
in the defendant's phone because of the evidence that it
contained -- incriminatory text communications with the victim
and codefendants. See Pratt, 915 F.3d at 270-271; see also
Cruzado, 480 Mass. at 284 (strong government interest justified
ten-day delay in seeking warrant where "police had probable
cause to believe that evidence critical to a recent murder was
present on the cell phone"). However, the defendant's
10 possessory interest in his phone was also similarly strong to
that in Pratt considering that he did not consent to its
seizure. See Pratt, supra at 272-273. Contrast Cruzado, supra
at 283-284 (minimal possessory interest in cell phone where
defendant disclaimed it belonged to him). Moreover, the phone
was not relevant independent of its contents. See Pratt, supra
at 273. Therefore, whether law enforcement was diligent in
obtaining the warrant becomes critical. See White, 475 Mass. at
594-595.
The Commonwealth argues the forty-day delay did not result
from a lack of diligence. It argues the complexity of the
investigation into the defendant and his codefendants, when
accounting for facts that the police were obtaining other
warrants and that multiple law enforcement agencies were
involved, justified the delay. We disagree. While "the nature
and complexity of the investigation" are factors in discerning
the reasonableness of a delay, Laist, 702 F.3d at 614, "[t]he
relevant inquiry . . . does not concern the detectives' general
diligence in performing their duties, but, rather, whether they
acted 'diligen[tly] in obtaining the warrant.'" White, 475
Mass. at 594, quoting Laist, supra.
Here, the UMass police did not act diligently in obtaining
a warrant once they seized the defendant's phone without his
11 consent. For instance, there is no indication from the record
that the police "put the ball in motion" soon after seizing the
phone by drafting or otherwise preparing the warrant affidavit.
Cf. Laist, 702 F.3d at 610-611 (twenty-five day delay reasonable
where law enforcement demonstrated diligence by beginning to
prepare warrant affidavit eight days after seizure and exchanged
drafts of affidavit with prosecution thereafter). In contrast,
the police appeared to be diligent in other matters involving
this investigation, as they applied for and obtained eight other
warrants two days after the defendant's phone was seized.6
However, the police failed to prioritize obtaining a warrant for
the defendant's seized cell phone. See White, 475 Mass. at 594-
595 (sixty-eight day delay in obtaining search warrant
unreasonable because police required to act diligently in
obtaining warrant and "it does not appear that they did so,
having instead focused on . . . applying for and executing five
other search warrants related to this case). See also Burgard,
675 F.3d at 1035 (prioritizing warrant "entail[s] diligent work
to present a warrant application to the judicial officer at the
earliest reasonable time").
6 UMass police seized the defendant's phone on October 17, 2012. On October 19, 2012, the UMass police applied for and obtained four search warrants (for the "bodies" of the defendant, Liccardi, Womack, and King) and four arrest warrants (for the defendant, Liccardi, Womack, and King).
12 Furthermore, the search warrant affidavit for the
defendant's phone did not establish there was anything complex
about drafting a warrant for digital forensic examination that
would explain the delay here. See United States v. Mitchell,
565 F.3d 1347, 1351 (11th Cir. 2009) (court found twenty-one day
delay in obtaining search warrant unreasonable noting affidavit
did not contend officer preparing warrant was unfamiliar with
background of child pornography investigation or that he lacked
sufficient knowledge to prepare affidavit). Nor does the record
reflect that the cell phone data extraction process was
particularly unfamiliar or difficult for the State police such
that additional preparation by the UMass police would be
required. In fact, the warrant appears to contain "boilerplate"
language concerning the phone's capacity to store data as well
as the extraction of such data.7 Once the UMass police obtained
the search warrant, a State police detective, who had previously
performed "at least [fifty]" cell phone data extractions using
the same software tool as he used here, extracted the cell phone
data from the defendant's phone in less than two days.
7 The affidavit was limited to the following language pertaining to extraction of data:
"I know that these various forms of data that are stored within cellular phones can be extracted from the phone. Extraction involves police making a copy of the data within the cellular phone."
13 Because the defendant maintained a strong possessory
interest in his phone, the police had an obligation to either
obtain a warrant without unreasonable delay or to return the
property; they did neither. After balancing the nature of the
intrusion to the defendant's Fourth Amendment interest in his
cell phone with the Commonwealth's interest in accessing the
phone's contents, accounting for the Commonwealth's lack of
diligence in obtaining a search warrant, on the record before
us, we conclude the forty day delay here was unreasonable. See
White, 475 Mass. at 593-594. Thus, the defendant has shown a
likelihood that a motion to suppress evidence recovered from his
phone would have been successful.
2. Reasonable probability of different verdict. To
prevail on his motion for new trial based on ineffective
assistance of counsel, the defendant must also show a reasonable
probability that the verdict would have been different without
the admission of the text messages that would have been excluded
but for counsel's incompetence. See Comita, 441 Mass. at 91;
Commonwealth v. Pena, 31 Mass. App. Ct. 201, 205 (1991). Such a
probability exists here due to the highly prejudicial nature of
the text messages that the jury never should have considered.
Specifically, the defendant's cell phone contained messages with
all three of his codefendants concerning the nature of their
14 encounter with the victim that supported the Commonwealth's
theory of the case and directly contradicted both of the
defendant's primary defenses at trial -- first, that he did not
take part in a joint venture to rape the victim,8 and second,
that his encounter with the victim was consensual. The
Commonwealth relied significantly on the text messages to show
the defendant's consciousness of guilt,9 as well as to establish
his willful participation in the joint venture to rape the
victim. Notably, the Commonwealth's theory of joint venture was
not limited to the element of aggravation, but also was the
basis for the underlying elements of the rape charges.10
8 The judge's final instructions to the jury concerning the Commonwealth's theory of joint venture included: "You have heard evidence of statements made in text messages purported to have been sent by Justin King, Caleb Womack, and Adam Liccardi. The Commonwealth offered that evidence against the defendant Bile to show his alleged participation in a joint venture."
9 The Commonwealth articulated its consciousness of guilt rationale for admission of the text messages in its motion to "Admit Defendant's Text Messages with Co-Defendants Post- Incident Reflecting Consciousness of Guilt"; the trial judge allowed the motion.
10The prosecutor expressly indicated this theory when, in response to the judge's request for clarity as to her proposed jury instruction concerning joint venture, responded: "I think once [the jury] ha[s] found a joint venture, that there was a joint venture, it is both, justifies a finding of culpability on the three counts [of rape] and it also justifies a finding of the third element for aggravated rape." The judge instructed accordingly with no objection from the defendant.
15 Consistent with its theory of proof, and to cast doubt on
the defendant's defenses, the Commonwealth emphasized the
defendant's text messages in its opening and closing statements,
and during its cross-examination of the defendant. For example,
in the Commonwealth's opening statement, the prosecutor offered
the text messages from the defendant to his codefendants to
demonstrate they had worked in concert, stating, "you'll see
those text messages between them . . . and you will see that
they wanted to take care of the [victim] situation, this problem
as fast as possible, and they agreed to pool the money to pay
her." The Commonwealth also relied on the text messages to show
the defendant's consciousness of guilt, telling the jury, "[you]
will also see [the codefendants] had several concerns,"
including "the possibility of surveillance cameras in the dorm."
During the Commonwealth's cross-examination of the
defendant, the prosecutor relied on his text messages to the
codefendants to provide damaging context to the statements he
made to the victim on the morning after the alleged rape
occurred. The prosecutor also confronted the defendant with the
text messages amongst him and his codefendants planning their
defense that the victim was blackmailing them, and in addition,
admitted that they would be "fucked" if the victim took them to
court.
16 The prosecutor, in her closing argument, again used the
defendant's text messages to demonstrate that he was part of a
joint venture to rape the victim, first by stating "look to his
own text messages" to show "[h]e's not the good guy and [his
codefendants] the bad guys. He's just as much a part of this
group . . . a part of what happened." The prosecutor concluded
her argument in part by emphasizing how the text messages proved
the defendant's participation in the joint venture as well as
his acknowledgment of guilt.11
The Commonwealth's reliance on the text message evidence
throughout the trial demonstrates its belief that this evidence
was highly persuasive in establishing the defendant's guilt.
Considering that the incriminating text messages related
directly to the elements of the offense, we conclude that there
is a reasonable probability the verdict may have been different
11The jury could have reasonably viewed the text messages as far more damaging that the defendant's admission in which he minimized both his shared intent with his codefendants concerning their trip to UMass as well as the acts he committed against the victim. For instance, the prosecutor argued:
"And if you need more evidence [that the defendant is as culpable as his codefendants] . . . look to his own text messages. Text messages he testified about yesterday, you'll have in writing. You can read those. He went there with the plan to fuck dem bitches, excuse my language. To put it in. To put it in the butt. That's what he's saying twenty-four hours before arrival there at UMass."
17 if such evidence had been excluded from the trial. See
Commonwealth v. Alvarez, 433 Mass. 93, 104 (2000) ("Where, as
here, the very matter as to which defense counsel has been
ineffective becomes one of the linchpins of the prosecutor's
closing, the defendant has met [their] burden of showing
prejudice"); Commonwealth v. Segovia, 53 Mass. App. Ct. 184, 193
(2001) (ineffective assistance where counsel's failure to move
to suppress evidence "opened the door to numerous negative
inferences against the defendant, all of which were explored in
the prosecutor's opening and closing"). A motion to suppress
the significant, illegally obtained contents of the defendant's
phone would have represented "better work [that] might have
accomplished something material for the defense." Commonwealth
v. DiGeronimo, 38 Mass. App. Ct. 714, 730 (1995), quoting
Commonwealth v. Satterfield, 373 Mass. 109, 115 (1977).
18 Conclusion. We reverse the order denying the defendant's
motion for a new trial. The defendant's convictions are
vacated, the verdicts are set aside, and the matter is remanded
to the Superior Court for a new trial.
So ordered.
By the Court (Massing, Hand & Smyth, JJ.12),
Clerk
Entered: April 16, 2025.
12 The panelists are listed in order of seniority.